Nitrogen → HCID 59687925, compound

HRID 444993

Reaction equation

HRID 444993 reaction equation
[C:1]([O:5][C:6](=[O:14])[C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=1)([CH3:4])([CH3:3])[CH3:2].[C:15]([O:19][C:20](=[O:47])[CH:21]([NH:34][C:35](=[O:46])[CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44]Br)[CH2:22][CH2:23][C:24]([O:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:25])([CH3:18])([CH3:17])[CH3:16].C([O-])([O-])=O.[K+].[K+].N#N>C(#N)C>[C:15]([O:19][C:20](=[O:47])[CH:21]([NH:34][C:35](=[O:46])[CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][O:13][C:10]1[CH:9]=[CH:8][C:7]([C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:14])=[CH:12][CH:11]=1)[CH2:22][CH2:23][C:24]([O:26][CH2:27][C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1)=[O:25])([CH3:16])([CH3:17])[CH3:18]

Participants

6

Reactant 4

HCID 947NitrogenHCID 11430Potassium CarbonateHCID 117640tert-Butyl 4-hydroxybenzoateHCID 59687918HCID 59687918, compound

Product 1

HCID 59687925HCID 59687925, compoundYield 110.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

4-Hydroxy-benzoic acid tert-butyl ester (0.65 g, 3.08 mmol) was dissolved in acetonitrile (7.5 ml) and added to 2-(10-Bromodecanoylamino) pentanedioic acid 5-benzyl ester 1-tert-butyl ester (1.62 g, 3.08 mmol). Acetonitrile (90 ml) and K2CO3 (0.64 g, 4.62 mmol) was added and the mixture was refluxed for 16 h under a flow of N2. The solvent was removed under vacuum. AcOEt (100 ml) was added and the solution was washed with water (2×50 ml) using sat. NaCl and methanol to aid phase separation, dried over MgSO4, and concentrated to yield a light brown oil (2.18 g). The oil was purified by flash chromatography (silica, 95:5 DCM/AcOEt) to yield an oil (160 mg, 8%).

Workup

  1. customThe solvent was removed under vacuum
  2. additionAcOEt (100 ml) was added
  3. washthe solution was washed with water (2×50 ml)
  4. customphase separation
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-685280ad0fbc4fcb9cd4dec5394b55cc
Source dataset
uspto-grants-2013_07
Patent number
US08476228B2

Linked notes

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